A.C.
Do you have Shopko in Illinois? We do in Wisconsin. I know they carry extrawide--not sure if that's wide enough for your son. I'm also not sure just how much they carry for small children. My 11 year old daughter wears extrawide, and that's where we've been getting her shoes (and sometimes boots) lately--but she is wearing women sizes.
You don't live very far from Madison, WI. In Black Earth, WI, right outside Madison, there is a little store called The Shoe Box that offers thousands and thousands of shoe/boot options (I try to go there a few times a year, just to look around). Google them, get their store hours, call and see what/how much they carry in your son's size, prices. I can't guarantee they will have much in the range you want to spend (that, I feel, is actually pretty cheap for boots. I feel in order to get a good brand/warm enough boot that you must start at least at $50-$60; the last pair I bought my daughter were Kamik adult size 10 extrawide, and they were in that price range.)
Have you tried Stride Rite? There's a store here in Madison in the Midvale Mall. We bought my daughter's shoes there until she grew out of kid shoes/began wearing adult sizes. I hated buying her shoes, because they were always $60 and up (because they were extrawide and not "normal" size). BUT we never had any issues with foot problems. Our Stride Rite store here in Madison has a card where after you buy so many shoes (you get punches), you get a free pair. Or something like that.
Unfortunately, your son has a very difficult size to buy (like my daughter) and will probably always have to pay more for his shoes/boots. Remember, we put a lot of stress and weight on our feet. Our feet carry our bodies around all day long. You need to make sure you put good, quality shoes on his feet. Cheap shoes will ensure that he has issues and problems with his feet or his ankles or his legs--problems that he could potentially deal with his entire life.
My husband's parents always bought the cheapest shoes/boots they possibly could for him and his brother. One summer, my husband had excruiating pain in his one foot/ankle/leg. His mom took him to the doctor. The minute the doctor saw what type of tennies shoes my husband had on, he ripped his mom a new one. He said, "You go out and buy this kid a pair of shoes that cost at least $50-$60 (back in the 1980s, that was a very good quality show/tennie), and I can guarantee you, his problem will go away." And the doc never wanted to see my mother-in-law bring him in again with the same issue. She went out, bought my husband a good quality shoe--and all his issues went away.
In terms of clothes buying, I will never stint on the cost of shoes. Yes, I put a ceiling on how much to spend. (Jimmy Choos? Please! NO ONE needs to spend that much money on one pair of shoes.) But I also make sure that what is being bought is of good quality. My daughter runs through the arches in her tennies quite fast, so halfway through the school year, I will cough up $50-$60 and buy her some arches made in Germany (or buy her another pair of brand new shoes). My husband needs leather dress shoes for work and doesn't like synthetic stuff inside them (makes his feet stink). He wears a 12EE and usually has to spend between $100 and $150 on each pair of shoes/boots he buys. Even buying tennies shoes runs him about $75.
It is what it is.
